Methyl 4-(bromomethyl)benzoate → Methyl 4-[(2-ethyl-5,6,7,8-tetrahydroquinolin-4-yloxy)methyl]benzoate

HRID 654370

Reaction equation

HRID 654370 reaction equation
[CH2:1]([C:3]1[NH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11](=[O:13])[CH:12]=1)[CH3:2].Br[CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1>>[CH2:1]([C:3]1[CH:12]=[C:11]([O:13][CH2:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=2)[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[N:4]=1)[CH3:2]

Participants

3

Reactant 2

HCID 256687Methyl 4-(bromomethyl)benzoateHCID 149504752-Ethyl-5,6,7,8-tetrahydroquinolin-4(1H)-one

Product 1

HCID 15171425Methyl 4-[(2-ethyl-5,6,7,8-tetrahydroquinolin-4-yloxy)methyl]benzoateYield 67%

Procedure

Using an analogous procedure to that described in Example 1, but starting from 2-ethyl-5,6,7,8-tetrahydro-4(1H)-quinolone and methyl 4-(bromomethyl)benzoate and purifying the product by flash chromatography eluting with methane/dichloromethane (1:49 v/v), there was obtained in 67% yield methyl 4-[(2-ethyl-5,6,7,8-tetrahydroquinolin-4-yloxy)methyl]benzoate (B), m.p. 79°-80° C.; NMR (CDCl3): 1.3(t,3H), 1.75-1.95(m,4H), 2.65-2.8(m,4H), 2.85-2.95(m,4H), 3.9(s,3H), 5.2(s,2H), 6.5(s,1H), 7.5(d,2H), 8.1(d,2H).

Workup

  1. custompurifying the product by flash chromatography
  2. washeluting with methane/dichloromethane (1:49 v/v)

Sources & evidence

ORD record
ord-0b5965b5c2c94078851b4b4bbcf03820
Source dataset
uspto-grants-1992_07
Patent number
US05130318

Linked notes

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